The saying "Free like the wind, not like free beer" is a version of the legal distinction known as gratis versus libre. It's an attempt to add some definition to one particularly slippery region of language. Free got complicated in the sixteenth century when it became attached to the monetary system, where it began to be used to denote transactions that took place outside of this system (free as in gratis; without cost).

In mid 1600s England, a small group emerged who began to undermine – literally – the institution of private property. Partly in response to rising food costs and a collapsing social order, the Diggers, led by Gerrard Winstanley, set themselves up to cultivate the common land, and live off what they produced. Winstanley set out his vision for a new society in a pamphlet called The Law of Freedom in a Platform (1652), a radical and eminently practical solution to the crises of his day.

As Christopher Hill writes, "Winstanley’s conclusion, that communal cultivation of the commons was the crucial question, the starting point from which common people all over England could build up an equal community, was absolutely right…. Winstanley had arrived at the one possible democratic solution that was not merely backward-looking, as all other radical proposals during the revolutionary decades – an agrarian law, partible inheritance, stable copy-holds – tended to be." The group was small and short-lived, and their community was constantly threatened by landowners and violent mobs, but they left a legacy of ideas which continues to fascinate and inspire.

The Diggers are undoubtedly the heroes of The World Turned Upside Down, Hill’s history of forgotten radical groups during the English revolution. He speculates about the "revolution that never happened" ("although from time to time it threatened") which would have produced a society based on communal property and a far wider democracy in political and legal institutions. And the Diggers’ undermining was as much about language as land. Without the institution of private property, the monetary notion of free (as in beer) collapses; the concept stops making sense.

Air and water – as in wind and beer – were also the focal points of a recent work by artist Natascha Sadr Haghighian, titled de paso (2012), seen at her recent quasi-retrospective at Carroll/Fletcher, London. The space was filled with the sound of crumpling plastic, a noise that persists impossibly (apparently via a small motor and algorithm) through a microphone dangling over an empty plastic bottle being slowly compressed by the handle of a plain hand-luggage flight case.

Here too, geography is key: in the next room Haghighian mapped the expansion of budget airline flight paths alongside documentation of Nestlé’s acquisition of the rights to bottle and sell water from St. Anne’s Well, Buxton (not to be confused with the water from the St. Anne’s Well in Malvern, which is bottled and sold by Coca Cola Enterprises as 'Malvern Water'). A solicitor's letter was pinned alongside, detailing the creeping corporate enclosure of this doubly free water; the letter itself, a freedom of information request, declined.

The freedom of information request suggests the weirdness of language in another popular technological slogan – "Information Wants to be Free." Does information want anything, and, if so, what kind of free is this? The phrase apparently originated in something Whole Earth icon Stewart Brand said at a hackers' conference in 1984, where he played on the double meaning: "On the one hand, information wants to be expensive because it's so valuable. … On the other hand, information wants to be free, because the cost of getting it out is lower and lower all the time."

Haghighian's art looks at the ways in which representational structures – language, for example – produce knowledge and behaviour. In a conversation with the artist, American physicist Evelyn Fox Keller notes a related equivocation of language: "Look at the word evidence, evidential. This already has a double meaning. It is made available explicit, available, visually available, but for the sake of something else." And words can carry a lot more than multiple meanings; Keller points out the heavy historical baggage of words, like the Enlightenment’s legacy in all our many sayings that connect sight and understanding ("Oh, I see" etc.).

Talking about words in this way is a little like Keller’s description of American scientist Barbara McClintock, "The scientist who looks through the microscope in order to understand how the mind’s eye shapes what we think we see with the retina." McClintock at her microscope, using one technology of representation to scrutinise another, analysing the way that these observations produce reality and how this reality becomes embedded in culture. In this tangled situation – the situation all creatures find themselves in – observer andobserved blur together, an infinite regress, or a pivot around which a system of knowledge, thought or organisation might be destabilised.

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I first encountered the wind/beer slogan in the context of free – like the wind – music, but it is more synonymous with the open source programming movement, used to distinguish freeware ("no charge") from freesoftware (free for public sharing and modification, without restriction). The connection between the ideals of the Diggers and digital politics is not a new one. During a covertly filmed conversation with Natascha Haghighian in a New York Whole Foods in 2008, Avery Gordon read A Declaration from the poor oppressed People of England directed to all that call themselves, or are called Lords of Manors, through this Nation; that have begun to cut, or that through fear and covetousness, do intend to cut down the Woods and Trees that grow upon the Commons and Waste Land – a Digger manifesto written by Gerrard Winstanley in 1649. The conversation was for a seminar intended to take place in the supermarket, if the supermarket had given permission; they didn’t, so it was filmed instead and posted online.

Gerard Winstantley

The Digger era was a time of unprecedented freedom of expression. Hill describes the "continuous flow of pamphlets on every subject under the sun ... For a short time, ordinary people were freer from the authority of church and social superiors than ever before, or were for a long time to be again... They speculated about the end of the world and the coming of the millennium; about the justice of God in condemning the mass of mankind to eternal torment for a sin which (if anyone) Adam committed; some of them became skeptical of the existence of hell. They contemplated the possibility that God might intend to save everybody, that something of God might be within each of us. They founded new sects to express these new ideas.... They attacked the monopolization of knowledge within the privileged professions, divinity, law, medicine. They criticized the existing educational structure, especially the universities, and proposed a vast expansion of educational opportunity. They discussed the relation of the sexes, and questioned parts of the Protestant ethic. The eloquence, the power of the simple artisans who took place in these discussions was staggering."

This newfound ability to publish widely and freely was crucial. Before the reformed monarchy clamped down on free presses in 1660, there was an explosion of dissenting religious and political pamphlets from Diggers, Adamites, Anabaptists, Baptists, Barrowists, Behmenists, Brownists, Familists, Fifth Monarchists, Free-will Men, Gindletonians, Jacobites, Levellers, Lollards, Muggletonians, Puritans, Quakers, Ranters, Sabbatarians, Seekers, and Socinians, as well as unaffiliated critics, madmen and visionaries (John Milton, for example). When Hill observed that during this brief time "it may have been easier for eccentrics to get into print than ever before or since" he was writing in a pre-Internet 1972. Of course now, forty years on, the very idea of "getting in print" has exploded beyond all recognition.

The dizzying circulation of words across contemporary networks, as well as crises of ownership and file sharing, suggest more unexpected resonances with the Digger era. In their book Cloud Time (Zero Books 2012), Rob Coley and Dean Lockwood suggest Winstanley as the unlikely "patron saint of cloud culture." In particular, they are referring to British writer Charles Leadbeater, who has recently begun championing Winstanley in support of a utopian “open cloud.” Against this interpretation, Coley/Lockwood argue that, "Leadbeater’s response to the end-time of the neoliberal project, juxtaposing the cloud commons with this eulogy to Winstanley, overlooks the fact that the digital commons is the new hunting ground for contemporary capital. Cloud culture is a product of post-9/11 disaster capitalism. Technological systems and ideas that were in their infancy prior to 9/11, merely lying around without coherence, were swiftly joined up and rationalized in a way that previously had been politically untenable." As Metahaven also continue to track in detail, the rise of cloud computing suggests a brand new form of enclosure, an increasingly privatised Internet with just a handful of conglomerate landlords.

In his writings, Winstanley also sometimes talked about clouds. They could also be ominous: in The Law of Freedom in a Platform he describes monarchical power as "the great thick cloud that hath hid the light of the sun of righteousness from shining in his full strength a long time," and in The Saint's Paradice (ca. 1648) he suggests, "It hath been the universall condition of the earth (mankind) to be over-spread with a black cloud of darkness." But elsewhere, he is prepared to accept the cloud and its ill effects: "The clouds send down raine, and there is great undeniable reason in it, for otherwise the earth could not bring forth grasse and fruit. … So that the mighty power Reason hath made these to give life and preservation one to another" (Truth Lifting Up Its Head Above Scandals, 1949).

Similarly, Metahaven are ambivalent about the cloud: "The political, legal and jurisdictional consequences of the cloud are slowly becoming apparent—right at the time when we are unlikely to withdraw from it. The cloud is just too good." At the same time they close with a cliffhanger, noting the basic materiality, the "lumpiness" of data: "The world indeed is lumpy enough for us not to draw easy conclusions. This story is not over yet. Tomorrow’s clouds are forming." There is a clear parallel between historical land enclosure and its creeping contemporary forms, but the obvious question – how does one dig a cloud? – is also a strange one. This is language out of control, a series of metaphors far too mangled. By contrast Winstanley’s insight was wonderfully straightforward: concentrations of power are intimately connected to buying and selling, to be undermined together; on or offline, free or otherwise.